Trans 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used for many applications including use as a refrigerant, blowing agent, solvent, cleaning agent and monomer for polymer compounds. The compounds of the present invention are part of a continued search for the next generation low global warming potential materials with low environmental impact.
Many methods are known in the art for making HCFO-1233zd (trans), most of them using three carbon starting materials which are obtained via multiple steps. For example, U.S. Pat. Nos. 5,777,184 and 6,472,573 describe the preparation of CF3CH═CHCl from CCl3CH2CHCl2 (240fa) with HF in the presence of a catalyst. Treatment of CF3CH2CF2H (245fa) and HCl at 280° C. with chromium catalyst is reported to give 1233zd (trans and cis), see EP 2327680. Reaction of CF3CH═CH2 with chlorine and HF affords 1233zd as one of the products; see WO 2008/54782 A1.
All of the above processes involve three carbon starting materials which in turn are made in multiple steps and thus there is a need to develop cost effective routes which utilize commercially available raw materials. The present invention addresses this issue by utilizing 3,3,3-trifluoropropene (FC-1234zf).